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Chemical Structure| 137-45-1 Chemical Structure| 137-45-1

Structure of 137-45-1

Chemical Structure| 137-45-1

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Product Details of [ 137-45-1 ]

CAS No. :137-45-1
Formula : C3H4N2O
M.W : 84.08
SMILES Code : O=C1NNC=C1
MDL No. :MFCD00629300
InChI Key :XBYRMPXUBGMOJC-UHFFFAOYSA-N
Pubchem ID :351317

Safety of [ 137-45-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 137-45-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 6
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 2.0
Molar Refractivity 21.41
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

48.65 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.5
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.27
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.3
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.68
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.42
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.14

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.81
Solubility 13.1 mg/ml ; 0.156 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.29
Solubility 42.9 mg/ml ; 0.51 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.03
Solubility 7.81 mg/ml ; 0.0929 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.0 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.13

Application In Synthesis of [ 137-45-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 137-45-1 ]

[ 137-45-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 34846-90-7 ]
  • [ 137-45-1 ]
YieldReaction ConditionsOperation in experiment
11 g With hydrazine hydrate; In methanol; for 2h;Reflux; Reference Production Example 1 (0548) A mixture of 21.1 g of methyl 3-methoxyacrylate, 10.0 g of hydrazine hydrate, and 20 mL of methanol was stirred with heating under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure to obtain 11.0 g of 1H-pyrazol-3-ol. 1H-pyrazol-3-ol (0549) (0550) 1H-NMR (DMSO-d6) delta (ppm): 10.22 (1H, s), 7.35 (1H, d, J=2.2 Hz), 5.43 (1H, d, J=2.2 Hz)
11 g With hydrazine hydrate; In methanol; for 2h;Reflux; The 21.1g of 3-methoxy-acrylate, and a mixture of 10.0g of hydrazine hydrate in 20mL of methanol was heated under reflux for 2 hours with stirring. The reaction mixture was concentrated under reduced pressure to obtain 11.0 g of 1H- pyrazol-3-ol.
  • 2
  • [ 137-45-1 ]
  • [ 35344-95-7 ]
  • bis(3-hydroxypyrazol-4-yl)-pyrazol-4-yl-methane [ No CAS ]
  • 3
  • [ 106-39-8 ]
  • [ 137-45-1 ]
  • [ 76205-19-1 ]
YieldReaction ConditionsOperation in experiment
80% With sodium hydroxide; In toluene; at 30 - 113℃; for 4.5h; After reducing the solution containing pyrazol in step (2) to 30 ° C, adding 45.18 g of toluene, stirring for 0.5 h, increasing the temperature of the mixture and refluxing the water to a moisture content of 0.08percent in the mixture. The temperature of the mixture was lowered to 40 ° C, 58.01 g (99percent, 0.3 mol) of p-bromochlorobenzene and 16.16 g (99percent, 0.4 mol) of sodium hydroxide were added, and the temperature of the mixture was raised to 110 ° C. After refluxing for 4 hours, the mixture was detected by liquid phase method multiple times. When the pyrazole peak disappeared, the reaction was stopped. After the temperature of the mixed solution was lowered to 40 ° C, 50 g of water was added to the mixture, and the mixture was dropped. Add hydrochloric acid to the pH of the mixture = 3, then raise the temperature of the mixture to 95 ° C, distill off the toluene, finally reduce the temperature of the mixture to 30 ° C, and suction to obtain 1-(4-chlorophenyl)-3-pyrazolol.Using this method, 31.96 g of 1-(4-chlorophenyl)-3-pyrazol was obtained in content of 97percent, yield 80percent.
 

Historical Records

Technical Information

Categories

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[ 137-45-1 ]

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